


P.S. I Love You

by 70sBabe



Category: Gilmore Girls
Genre: F/M, Literati, for once in their dramatic lives, good old fashioned letter writing, soft jess, soft rory, they're meeting each other halfway, what if rory actually wrote that letter to jess while she was in dc?
Language: English
Status: Completed
Published: 2019-03-28
Updated: 2019-03-31
Packaged: 2019-12-25 20:02:08
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 8,296
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/18268403
Author URL: https://archiveofourown.org/users/70sBabe/pseuds/70sBabe
Summary: A journey of self-improvement, dating advice, and book recommendations.set between seasons 2 and 3





	1. June

Dear Jess,

Hi. How’s your summer going? I bet Luke’s got you working 24/7 at the diner, huh? He means well, you know. He just wants to keep an eye on you. What about books? What are you reading? Right now, I’m reading _Murder on the Orient Express_ . It’s my first Agatha Christie and I know it’s cliche to start with _Murder on the Orient Express_ , but it’s good, so who cares? I finished _The Sun Also Rises_ a few days ago and you know what? It wasn’t half bad. That’s the first time I’ve ever spoken so highly of a Hemingway novel. Are you proud of me?

Anyway, I just wanted to see how you were doing. Not to rub salt in the wound or anything, but I know you don’t have a lot of friends in Stars Hollow, so I thought you might need someone to talk to. I hope you’re doing good.

 

Sincerely,

Rory

______________________________________________________________________________________________________________________________________________

 

Dear Rory,

Nice try, but you’re not getting off that easy. You kissed me, remember? That means something. I know you don’t care what shifts I’m working or if I’m reenacting The Sandlot with the high school dopes. You do care about what I’m reading, though, so I’ll tell you. Sherlock Holmes. Guess we’re both on mystery kicks, huh? And yeah, I am proud of the Hemingway praise. Just because you don’t immediately love something doesn’t mean it’s bad or worthless. Pass that message along to your mom, okay? With all the evil eyes she’s giving me, I think I’m on the verge of being hexed.

Talk to me, Rory. You kissed me. I didn’t kiss you (well, not until you made it abundantly clear that you wanted me to kiss you). Tell me what you’re thinking. Maybe I’ll do the same. A tempting offer, right?

 

-Jess

_______________________________________________________________________________________________________________________________________________

 

Dear Jess,

God, that is just so typical of you! All you want to talk about it the stupid kiss! And it _was_ stupid! I can’t believe I did it and yes, I am taking full responsibility. You haven’t told anyone, have you? Because if you have, I’ll sic Lorelai on you. She’ll have my full support in hexing you.

 

Sincerely,

Rory

 

P.S. I finished the Christie. I’m rereading _Walden_. Guess I miss small town life more than I thought I would.

________________________________________________________________________________________________________________________________________________

 

Dear Rory,

The fact that you don’t wanna talk about the kiss tells me that it meant something to you, but instead of pressing the issue, I prefer to rest on my laurels, tiny and insignificant as they may be.

I don’t think Thoreau was picturing the Stars Hollow funny farm when he said, “I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived.” He was picturing a little more solitude, a little less Kirk, you dig?

But I know what you mean. I miss New York sometimes, but it’s not as bad as I thought it would be. The missing it, I mean. Sometimes, I think I might actually like Stars Hollow, and not just for the endless opportunities for entertainment it provides. It’s nice to have people know you, to have people you can rely on. Of course, as the town ne'er-do-well, I don’t exactly get the same treatment as everyone else, but who’s fault is that? Mine. If you tell anyone I said all of this, I’ll kill you.

 

-Jess

 

P.S. still slogging through Sherlock Holmes; geez, that Arthur Conan Doyle didn’t know how to just let a good thing go. I’m rereading _Walden_ , too, if you couldn’t tell from the above quote.

_________________________________________________________________________________________________________________________________________________

 

Dear Jess,

Wow, I’m saving that last letter, for sure. The next time you start humming the Green Acres theme song under your breath, I’m pulling it out to do a dramatic reading. I mean, Jess Mariano, admitting that he likes Stars Hollow? It’s Twilight Zone-esque.

All joking aside, I’m glad you’re starting to feel more at home there. You know, if you got rid of the whole chip-on-the-shoulder bit and started smiling a little more, you’d get the full Stars Hollow treatment. I know you think that being nice is just a means to an end, another way to get what you want, but most people just want to be nice to others.

Remember when you came over to my house for dinner? And you and my mom got in that huge fight that I’m still not really sure was about? She wanted to be nice to you. She wanted to make you feel better about being in a strange house with strange people in a strange town. If you had just met her a fourth of the way (I know halfway is still way beyond you), you would have had an ally for life.

And I know you’re rolling your eyes as you read this, and I know that your next letter will probably include some line about putting away my pom poms, but you know it’s true. Just try being a little nicer to people, okay? Start small. Something nice for Luke. Or smile at customers when you take their orders! I think it’ll make you feel better, too.

 

Sincerely,

Rory

 

P.S. I let Paris borrow my copy of _Franny and Zooey_ and she raised holy hell about the notes in the margins. She thinks you’re a delinquent of the highest order.

_________________________________________________________________________________________________________________________________________________

 

Dear Rory,

Well, I took your advice. I started smiling at people. And, boy, did it backfire! All that Emily Post-ing I was doing convinced Taylor that I was reformed and could now take part in town activities. He tried to get me to run the cotton candy machine for the big Flag Day extravaganza they’re putting on and I couldn’t help it. I told him hell would freeze over before I agreed to distribute crystalized sugar to the crackpots around here and….well, I guess you could say all the goodwill I’d built up disappeared in the blink of an eye. Of course, you did say to do something nice for Luke and the amusement he got from the whole situation will be Chicken Soup for his Soul for many years to come.

I talked to your mom a few days ago. I didn’t tell her we were writing. I didn’t know if she knew and I didn’t wanna get in the middle of things with you Gilmores. I did my best to be civil and we didn’t do the usual snappy insults bit, so maybe I’m making some headway there. She even smiled at me. Luke’s head almost exploded.

Are we ever gonna talk about the kiss? I mean, more than you just getting all huffy and writing me a one-paragraph letter. We don’t have to talk about anything more than that one kiss. Nothing about the future. Just that one kiss. I just wanna know why you did it, Rory. I’m kinda going crazy over here, which, I guess, is helping me fit into this town.

 

-Jess

_________________________________________________________________________________________________________________________________________________

 

Dear Jess,

God, I wish I’d been there when you told Taylor off. Was Mom there? I’ll get her to give me a play-by-play. Don’t let this discourage you, though. I mean, you don’t have to kiss any babies or anything; just show a little common courtesy. I think it’ll make things so much easier for you and if there’s one thing you need, it’s easy.

The kiss. What is there to say? That I temporarily lost control of myself? That I didn’t know what I was doing until my mouth was on yours? That I don’t regret it? Well, I’m not sure about that last one. I keep flipping back and forth on the regret thing. I shouldn’t have kissed you. You know that, too. And I’m still with Dean. And if you weren’t such a jerk about all things pertaining to Dean, I would probably want to talk about him with you. I like talking to you. You always have new ways of looking at things and you’re not as judgemental as my mom is sometimes. Things with Dean are messy and he doesn’t even know they’re messy, you know what I mean?

I’m not trying to give you any hints or false hope. I’m still with Dean and I want it to work with him. I love him. I know that’s not what you want to hear, but it’s the truth.

 

Your friend,

Rory

 

P.S. Have you ever read _Wuthering Heights_? I think you would like it.

_______________________________________________________________________________________________________________________________________________

 

Dear Rory,

I’m a jerk, I know. Not just about Dean, either. I’m just a jerk most of the time. It’s who I am. But not with you. So, if you wanna talk about Dean, talk about him. I can’t promise that I’ll give you helpful advice or that I won’t ask questions that are designed to annoy you, but I’ll listen. Read. Whatever.

Luke thinks I’ve been replaced by a pod person. Or that I’m gonna rob the diner. Or that I’m gonna burn the diner down. Pretty much any form of vandalism is on the table. He keeps asking me what kind of game I’m playing and he doesn’t think it’s funny when I say Monopoly. Your mom does, though.

Hey, tell me about D.C. You’re at our nation’s capital, rubbing elbows with all the policymakers, and yet you wanna talk to me about the power of positive thinking. Have you been to the Smithsonian? I’ve always wanted to go there.

 

-Jess

 

P.S. I noticed you upgraded me from “sincerely” to “your friend.” Are you trying to tell me something?

P.P.S. _Wuthering Heights_? Don’t make me laugh.

_______________________________________________________________________________________________________________________________________________

 

Dear Jess,

D.C. is cool. It’s weird; the parts that aren’t government buildings and museums are all funky coffee shops and vintage stores. I don’t get to see too much of that other side, though. When I’m not in seminars or listening to speeches, I’m going over debate notes with Paris, or quizzing her on all the members of the Cabinet. I’ve tried to teach her the value of a little good manners, too, but she’s not taking to it the way you are.

Speaking of that, how goes the courtesy crusade? Are you and Luke wearing friendship bracelets yet? Has Taylor roped you into being the grand marshal of the Fourth of July parade? And hey, what was with that one line about my mom thinking you’re funny? Are you guys friends now? Or friendlier, at least?

Now that I’ve exhausted all other topics, I guess it’s time to turn to Dean. He’s just…..he’s so great. He cares about me so much; the only times we ever really fight are when he thinks I don’t care about him as much as he cares about me. I love him and I don’t know why he can’t see that. There’s a lot of things he can’t see, as a matter of fact. He can’t see beyond Stars Hollow or our senior year. He can’t see a bigger life than the one he has now and I don’t know why. I always thought that everyone had dreams, even if they were impossible and never going to happen. Lane and I used to spend hours talking about the things we would do when we grew up, the places we would go, the people we would meet. I love Stars Hollow, but the world is so much bigger, you know? If Dean and I stay together while I’m at college (I refuse to say Harvard, I don’t want to jinx it), he’ll start to feel pushed to the side. He already does by me being at Chilton. I just don’t know how to explain….well, I don’t even know what I want to explain to him. I guess I just want him to try and get on the same page as me. I know that’s not fair to ask that of him, but it’s what I want.

Give me some advice, Dr. Phil. And keep the sarcastic commentary to a minimum, please.

 

Your friend,

Rory

 

P.S. I upgraded you to “your friend” because I feel like we’re actually talking now, which is what friends do. Don’t make me take it back.

 


	2. July

Dear Rory,

So there’s a lot of things Dean can’t see, huh? I’m guessing it’s because he’s too far away, him being the height of Frankenstein’s monster and all.

Okay, now that I’ve gotten that out of my system: Dean doesn’t think the way you do. Most people at Stars Hollow High don’t think the way you do, myself included. You’ve always had a Plan with a Capital P and that Plan always included college and a steady job and enough pocket change to take a weekend jaunt to Paris or Rome or wherever. You dreamed big because Lorelai wanted you to dream big. She wanted you to be more than a statistic. I mean, daughter of a single, teen mom gets into Harvard and then becomes a war correspondent? Who could tell Lorelai she ruined her life after that?

Now here’s the part where I say something you don’t wanna hear, but I’m gonna say it anyway, because someone has to. As much as Dean tells you he digs the smart chick thing, that’s not what he wants. He wants what his parents have, which is a nuclear family and a wife that has dinner on the table at 6:15 sharp. He likes his life, he likes his parents’ life, and he doesn’t see any reasons why he should try for anything bigger. And there isn’t anything wrong with that. We can’t all be the main character, Rory. Some of us are just bit players in this thing we call life. So (God, I can’t believe I’m saying this), cut Dean-o some slack. He doesn’t get you, either. But he loves you, and, based on all the books I’ve read, I believe that’s all that matters. Opposites attract, and all that.

Things with Luke are good. He doesn’t have that permanent furrowed brow anymore, which is good, because he’s one long rant away from a heart attack. And funny that you mentioned the Fourth of July parade because I did, in fact, attend. Not in any official capacity, but I thought I’d see what all the fuss is about. I even helped Miss Patty set up her snow cone booth. Do I get a sticker? Time off for good behavior? Because I gotta tell you, I’m being a really good boy, I swear.

Your mom is warming up to me. Probably because I sneak her coffee, even after Luke tries to cut her off. She noticed me reading _Anna Karenina_ and told me that’s one of your favorites. I pretended I didn’t know that because I thought it might foster conversation between us and boy, was I right. We talked for a solid 8 minutes (yes, I clocked it). I told you I’m being a good boy!

Tell Paris to take a chill pill. Has she ever had fun in her life? When you guys get back, bring her to the diner. I finished _A Tree Grows in Brooklyn_ last week and I wanna know her opinion. Oh, alright, you caught me: I wanna argue over Smith’s simplistic language and predictable plotline. I’ll be pro, Paris will be against. Tell her I’ll even let her use the counter as a mock podium. Luke’ll go ballistic.

 

Your friend (because I am, you know),

Jess

_______________________________________________________________________________________________________________________________________

 

Dear Jess,

Wow. When I asked for Dr. Phil, I didn’t think I’d actually get him. When did you become so insightful? Are you reading self help books or something? Catching Oprah reruns? Okay, I’ll stop ribbing you and just say: thank you. I know you don’t like Dean, but you gave me some good advice. Even if it did sort of make me mad. Why did it make me mad, you ask? Because you’re right, and I hate it when you’re right! It’s a good thing we’re doing this in letters because if I had to see the self-satisfied smirk on your face as you delivered this diagnosis, I would scream. I practically did while reading your letter. Paris thought I had finally lost the last of my marbles.

With all these good neighbor stories you’re telling me, you’re getting a whole book of stickers. Gold star ones. Keep it up and I’ll bring you a snowglobe. Not that I don’t like that you’re making an effort to assimilate into society, but….well, what brought this on? Why the sudden need to turn over a new leaf?

I think Paris would love a good debate. She needs someone who can keep up with her in the arguing department. She’s already terrorized 12 senators. I think she’ll hit ‘em all before it’s time to go home. Home. I miss it. How are things going there? Anything crazy happen? Well, crazier than you and my mom actually having conversations. The coffee sneaking is a stroke of genius. Keep that up and she’ll invite you over for Christmas.

 

Your friend,

Rory

______________________________________________________________________________________________________________________________________

 

Dear Rory,

What brings on my sudden need to turn over a new leaf, you ask. I wanna accuse you of playing dumb, but I know you’d never do that with me. It’s you. Partly. It’s also Luke. And that I got a little tired of wearing the black hat. Playing the villain is only fun when you have a moustache to twirl and I’m a few years away from impressive facial hair.

I guess I just wanted to make things easier for the handful of people who are in my corner. I hate that you fight with your mom about me. I hate that everyone gives Luke crap for keeping me around. I figure playing nice will get some of the townsfolk off you guys’ backs. Geez, this place really is changing me. Can’t remember the last time I did something selfless. Well, there goes my _Rebel Without A Cause_ bit. Think I can still get by with a Dylan McKay act?

Have you ever read anything by Carrie Fisher, a.k.a Princess Leia? She’s a riot, but sometimes in a sad way. “I feel I'm very sane about how crazy I am.” Doesn’t that describe literally everyone in the Hollow? It sounds like something Lorelai would say. I’d send you my copy of _Wishful Drinking_ , but it’s currently out of my hands, and I mean that literally.

Hey, wanna hear something crazy? Andrew started giving me a store discount. He says with you gone, I’m his best customer. Better get back soon, Gilmore. I’ll move into your room next.

 

-Jess

______________________________________________________________________________________________________________________________________

 

Dear Jess,

Oh, my God, you didn’t. You lent a book to my mom!!! And don’t try to deny it, because she as good as told me. I mean, what are the odds that, right after I get your letter, Mom casually mentions that she’s been reading _Wishful Drinking_ and that she thinks I’d love it? Are you and Lorelai in cahoots? God, you really are taking my place. September can’t come soon enough.

I’m reading _The Boys on the Bus_. It’s about political reporting in the 70s. The guy who wrote it was Hunter S. Thompson’s protege. Maybe I’ll send you a copy. Oh, alright, you caught me: it’s already in the mail. I expect you to return the favor!

Now, to talk about the heavy stuff. I think Dean’s gonna come visit soon. He keeps mentioning it when we talk on the phone and, even when I tell him things are super busy here, I can tell he thinks I’m lying. And before you ask, no, he doesn’t know we’re penpals. Sometimes I wonder if it’s worth it. Keeping all these secrets from him, I mean. I feel like I’m always tiptoeing around things but pretty soon, there’ll be too many secrets and not enough room to sneak through. Does that make sense? I don’t know what to do. I know I should talk it over with my mom but it took her so long to warm up to Dean and now she really likes him. She also thinks you’re still trying to break us up. Well, at least, I think she does. Now that you guys are sharing books, her opinion of you might have changed. Wow, I never thought I’d write that sentence.

I liked hearing that you’re being good to make things easier on people, me included. I know you’re a good guy and it always annoyed me that you tried to keep that a secret from everyone else. I know you’re squirming because I said you were a good guy, so I’m gonna say it again. Jess Mariano, you’re a good guy. A good person. Sure, your halo is a slightly tarnished, but it’s still there.

 

Your friend,

Rory

_____________________________________________________________________________________________________________________________________

Dear Rory,

Don’t worry, me and Lorelai aren’t gonna be roomies any time soon. I get the feeling she’s just waiting for the other shoe to drop, but things have been peaceful between us so far. Stars Hollow misses you, too. It’s weird not seeing you waiting at the bus stop or sitting in the diner or walking with your mom across the town square. Like there’s a puzzle piece missing. And it sucks not being able to talk to you. Well, at least we’ve got the letters.

Which, I’m not surprised, you haven’t told Dean about. He’d flip his lid. He practically blew a gasket that time he caught me at your house. I mean, Paris was there the whole time! What did he think we were doing? And I get it, it sucks to have to keep things from him. So maybe you shouldn’t. Try telling him the truth once in awhile. Maybe if you give him a chance to accept stuff, he won’t get mad because you’re lying. Does that make sense? You shouldn’t be with someone you don’t wanna tell stuff to. Talk to Lorelai about it. She’s good at this stuff, right? Just don’t mention me. I don’t want all my brownie points with her to be swept away. Back to Dean: maybe a visit would be good for you guys. You can talk in person about everything you’re feeling and, since I’m a couple hundred miles away, he can’t blame any of it on me.

I mailed you _Postcards From the Edge_ . A different Carrie Fisher (your mom still has _Wishful Drinking_ ). I like having someone to share books with. No one else really gets it, you know? I mean, even though we don’t always like the same books, I know your opinion is informed, at least. And I like looking at things from your perspective.

 

-Jess

 

P.S. Silly Rory; I sold my halo for scrap metal years ago.

____________________________________________________________________________________________________________________________________

 

Dear Jess,

Well, Dean is coming. Next weekend. I’m excited to see him, I am, but….well, there’s all this other stuff to talk about and I don’t know if I want to do it now or later. I mean, why get into a huge discussion about our futures the summer before senior year? We have all of senior year to do exactly that. I know you’re groaning as you read this and you’re right, you’re right: I’ll say what I need to say to him. I just hope he won’t think I’m breaking up with him.

My mom told me she saw you helping Babette carry her groceries home. She also said that when you noticed she was watching from our porch, you basically sprinted out of there. Get used to being a good boy, Jess Mariano! I need someone to share the title of Golden Child. The crown gets heavy after a while.

I know I already used up my allotted Dean paragraph, but I’m still freaking out about it. What if he breaks up with me? What if I hurt his feelings, or he gets mad? I just want things to stay the same. I hate change. And I don’t know what I want and I think maybe some people are getting caught in the crossfire. Dean. My mom. You.

I’m afraid I’m hurting you, Jess, and I know if you were here and we were having this conversation in real time, you’d say something like “Ah, you can’t hurt me, I’m made of titanium” and you’d play it off, but everybody gets hurt. You’re my friend, a really good friend, and if I ever hurt you in anyway, please tell me. Seriously.

 

Your friend (really and truly),

Rory

___________________________________________________________________________________________________________________________________

 

Dear Rory,

You said something in one of your previous letters about me seeing kindness as a transactional thing and sometimes I worry that you’re right. Too much time with my mom, I guess. Her name is Liz and she’s…..difficult. Sometimes I think her brain froze at 21 and she hasn’t matured since. I can’t even really get mad at her for anything because she just doesn’t seem to know any better. Life is all about what you can get from other people, in her eyes. Mine, too, I guess.

I’m bringing this up because you said you were afraid you might be hurting me. You might be. I honestly can’t tell at this point. But that’s not the point. The point is that I’m afraid I’m hurting me, too. I’m afraid I’m only doing this whole Opie routine because I know it makes you happy and I like making you happy. But you know why I wanna make you happy and it’s not just because we’re such swell penpals.

I think maybe we should stop writing for a little bit. I need to get my head on straight and figure out what I’m doing and why I’m doing it. I don’t wanna end up like Luke, you know? Pining after some girl who’s never gonna look at him like that, pulling himself apart and putting himself back together just so she can smile. I can’t live like that. I won’t live like that.

I’m sorry, Rory. I know you like talking to me. I like talking to you, too. Probably more than I should. I hope you understand.

 

-Jess

___________________________________________________________________________________________________________________________________

 

Dear Jess,

I get it. I wish you didn’t feel this way, but it’s out of my control. I hate that. I hate when things are out of my control. I think that’s why I’m having so much trouble with Dean. He gets here tomorrow and I still don’t know if I’m going to launch into the speech I’ve rehearsed a thousand times or just kiss him and pretend everything is fine. But you don’t want to hear about this, do you? God, who am I kidding? You probably threw this letter away as soon as you got a good look at the return address. But I need to feel like I’m talking to you, even if you’re not talking back, so go ahead. Shred my letters. I deserve it.

You’re not like your mom, Jess. You’re smart and you’re definitely mentally past 21 already, and you want to change. At least, I think you do. Write to me if you think you’re up to it. I need you in my life and I know that’s not fair. I know what loving my mom has done to Luke and I hate that for him, but that’s not you and me. We won’t let it be us.

 

Your friend,

Rory

___________________________________________________________________________________________________________________________________

Dear Jess,

Please call me back, please, I need to talk to you. Or write to me. Smoke signals. Something. I left you alone for long enough, okay? Everything is a mess and I need you. I need you. I need you.

 

Your friend,

Rory

 


	3. August

Dear Rory,

Geez, I leave you alone for 2 weeks and you set the whole world on fire, huh? Okay, okay, I know I shouldn’t be joking around. I thought it might lighten the mood.

You were a mess on the phone, Gilmore. I hated hearing you like that. And I swear, if Dean wasn’t in Chicago right now, I’d kick his ass all the way to the Pacific. He shouldn’t have said any of those things to you. He shouldn’t have made you cry. He shouldn’t have broken up with you, either, but that’s his loss.

You didn’t do anything wrong, okay? You tried to have a mature discussion about the future with him and he flipped. This isn’t your fault, so don’t beat yourself up over it.

I wish I was in DC with you. Or you were here with me. Or we were anywhere else together. I hated hearing you cry on the phone and knowing the only thing I could do was throw out generic sympathetic comments. If you were here, I would’ve been able to hug you or something. I’m not too good with physical affection, so give me a break, huh?

I sent you some books. Recommendations that I wanted to give you while we weren’t talking. Writing. Whatever. I hope they take your mind off things. And tell Paris to cut you some slack, too. I’m worried about you, okay? I admit it. Me and Lorelai should start a support group. Write me back ASAP.

 

Your (worried) friend,

Jess

___________________________________________________________________________________________________________________________________

 

Dear Jess,

Don’t worry about me, okay? I’m fine and I get enough concerned phone calls from my mom. I don’t need you to start in, either.

I bet you’re loving this. You were right all along, about me, about Dean, about how it would all crumble before our very eyes. I hate when you’re right. I know I sound mad at you right now, but I’m not. I’m just….processing. It’s a lot to process, you know. He was part of my life for so long and now I’m going to go home at the end of the summer and he won’t be waiting for me. He won’t buy me coffee after school or take me to movies. He won’t make fun of me for not knowing who Joe Namath is. He won’t be around to change the water bottle. God, what is Mom gonna do now?

Thanks for the books, by the way. You’re on a real Stephen King kick right now, huh? _Different Seasons_ is my favorite so far, but that’s just because Shawshank Redemption is one of my favorite movies ever. I also appreciated the copy of _The Bell Jar_ , even though I know you know I already own it. Don’t worry, I’m not going to take any cues from Esther Greenwood.

 

Your (perfectly fine) friend,

Rory

 

P.S. If you wanted to call me some time, that would be okay. I mean, since you have the number already. But only for emergencies, alright? I’m a very busy woman. I can’t be fielding your calls at all hours of the day and night

 

P.P.S. Thank you

__________________________________________________________________________________________________________________________________

 

Dear Rory,

This town is bonkers, you know that, right? I mean, just when I think I’m getting used to the controlled madness, Taylor announces the next inane town gathering and my mind is left spinning in confusion. Guess what we’re celebrating next week? Go on, guess.

Oh, alright, I’ll tell you. National Lemonade Day. A whole festival….for a beverage. Luke practically turned purple when he saw the flyers. I don’t get why he’s not used to it by now. He’s lived here his entire life. Nothing should surprise him anymore.

I know this’ll knock your socks off, but guess who I bought some CDs for yesterday? That’s right, the one and only Lane Kim. I feel bad for her. Her mom is the definition of a dragon lady. It’s not like Lane even wants to do anything super crazy! She just wants the latest Pixies single and her mom acts like Lane wants to start smoking crack. At least Luke knows not to regulate my media consumption. If he ever started laying down the law like that, I’d be….well, I was gonna say I’d be gone in a flash, but maybe I wouldn’t. I don’t know where I would go. New York, sure, but I don’t wanna go back to my mom. I don’t know why I’m even thinking about this, because I’m not going anywhere. And I know you’re rolling your eyes and saying “yeah, right,” but I promise I’m sticking around. For the foreseeable future. After senior year, though, who knows?

So, I heard through the grapevine that Dean is getting back to Stars Hollow next week. Want me to deck him for you? Just a little black eye, maybe a split lip, nothing major! It would make you feel better, I promise. It would make me feel better, too. I’ll probably call you tomorrow, which means we’ll have talked before you even get this letter, but that’s okay. I just have to keep talking to you. As long as I keep talking to you, I don’t even think about running. And I’m really tired of running, so you’re doing me a hell of a favor, Gilmore.

 

-Jess

 

P.S. Don’t worry, I changed the water bottle on Tuesday. Lorelai gave me a Twinkie for my services.

 

P.P.S. You’re welcome

________________________________________________________________________________________________________________________________

 

Dear Jess,

It’s good to hear your voice, especially when I’m capable of giving coherent answers instead of just wailing into the phone. Okay, wailing might be an overstatement, but that’s what it felt like. I just can’t believe it. I didn’t want to break up, you know that more than anyone. I just keep thinking about what Dean said: “I know you think you’re better than me” and “I’m tired of nothing being good enough” and “We’re not all like you, Rory.”

“We’re not all like you, Rory.” Huh. Isn’t that what you told me a few weeks ago? Seems as if you and Dean were more connected than I was. I keep waiting for him to call me and tell me he made a mistake. Not that I want him to or anything. He just seems like the type to break a toy on purpose and then get upset that he can’t play with it anymore. Does that make sense? I feel like we’re always asking each other that and I don’t know why. Everything you say makes sense to me and you haven’t seemed to fall behind on anything I’ve said, either. Kindred spirits. That’s what we are. Like best friends, but different, because we’re too much alike. Ugh, I’m getting all introspective and annoying. Fitzgerald does that to me (I’m in the middle of _The Beautiful and Damned_ ).

I’m glad someone’s keeping Lane in bootleg CDs while I’m gone. Her contact with the outside world is tenuous at best. She needs someone to keep her connected. God, if you guys become friends, you’ll have officially filled my shoes in Stars Hollow. All jokes aside, I want you and Lane to be friends. When I get home, we’ll be like the 3 Musketeers. Or something. It’ll be nice. You know, as long as you stick around. I’m serious, Jess, don’t leave again. I don’t know if I can chase you anymore. I also don’t know if I can take another bus ride. Those things were seriously gross!

Don’t do anything to Dean, I mean it. For one thing, it won’t earn you any brownie points from the rest of the town. You’re doing better, but Taylor is always on the lookout for bad behavior. For another, I don’t think it’ll make me feel better. Okay, that’s a total lie, but I want it to be true! And I refuse to encourage violence! Don’t need that getting back to the Harvard admissions board, now do I?

I don’t know if I’ve said this lately, but you’ve really changed, Jess, and in the best ways possible. Who knew that all it would take to get you straightened out was for me to ship off for a couple months? Maybe I should just stay in DC. You’d be applying for sainthood before the year is out. Just something to think about….

 

Your friend,

Rory

_______________________________________________________________________________________________________________________________

 

Dear Rory,

You’re kidding, right? There’s no way I’d trade your absence for sainthood. Which one do you think I get more enjoyment out of? Come home so you can hear the glowing accounts of my good deeds. Also, your mom needs someone to bounce material off of; Luke can only take so much of her nonsense. And, before you say anything, I do my best to keep up with her, but I can only take so many Duran Duran references. Your mom takes 80s mania to a whole other level.

I got a job. A new one. I’m still working at the diner (Luke would freak if I took off on him), but when I’m not there, I’m working at the bookstore. Yep, you read that right: the bookstore. It’s nice to spend the day surrounded by books and very few people. You play your cards right and I’ll let you use my employee discount.

Now to get serious. Yeah, we’re not all like you, Rory, and that’s a good thing. You’re special. You’re different. You’re gonna do something, be someone. Don’t let some dumbass comments from your dumbass ex rattle you. Talk to Paris about it. I can see her actively and passionately defending you and your dreams. Hell, she’ll probably kick Dean’s ass for us. You and Dean just weren’t….on the same page. You were barely even on the same chapter. It’s for the best for both of you that you ended it now before something really crazy happened. I mean, I may be an honorary Boy Scout now, but I’m not above using a little subterfuge to seduce a beautiful girl.

I know I sound like a broken record, but I miss you, Gilmore. Yeah, I’ve got more people to talk to now (who knew being nice would get you some pals?) and sure, I’m keeping busy (working two jobs and all), but I miss you. I need to talk to you, and not on the phone. In person. About everything. I’m trying to be delicate about the whole situation, but you know how I feel. I hope I didn’t completely freak you out with all this.

 

-Jess

 

P.S. _Boys On The Bus_ was good. Now I’m reading all the Hunter S. Thompson I can get my hands on and right now, that’s _The Rum Diary_. I’ll tell you how it goes.

______________________________________________________________________________________________________________________________

 

Dear Jess,

You’re working at the bookstore?!? Lucky! From now on, you’re supplying all my literary needs. I mean, an employee discount at a bookstore? Were sweeter words ever spoken? I’m glad you’re keeping yourself busy. That’s what’s been so great about D.C. No time to think about anything but the task at hand. Paris has been a godsend, too. You got her exactly right. When I told her what happened, she immediately launched into a tirade on how men only want Malibu Barbies and any woman worth her salt would just stay single her entire life. A bleak outlook, but she does make some valid points.

What about you, Jess? Do you want a Malibu Barbie type? I’m trying to diffuse the tension, which is crazy, because how can there be tension in a letter? We’re not standing in front of each other or looking each other in the eyes. I don’t know if that would make things easier or harder. I do know how you feel, Jess (you’ve never really kept it a secret), but you’re right. We need to talk in person. I _want_ to talk in person. I miss you, too, and it’s weird because, at the beginning of the summer, if you had told me I’d be yearning to see Jess Mariano in the flesh, I’d have thought you were crazy! I still sort of do. Think it’s crazy, I mean. Because isn’t it? Not to you, I’m sure. You’ve been focusing on this for the last 9 months or so. Which scares me. You seem so sure of me, of everything. How do you know? How do you know this is what you want? How do you know this is what we need? I don’t really want to talk about this anymore. Not until we’re both in the same place. It doesn’t feel real when we talk about it like this and nothing about you and me should feel artificial.

Oof, that was heavy. I wish we could talk about average teenager things, but I’m guessing adolescent romance _is_ what average teenagers talk about. Tell me about what’s going at home. Mom mentions you more and more and I finally let it slip that we’ve been writing to each other. All she said was “You know, I had a feeling you two were talking.” How does she always know everything? Must be a mom thing.

 

Your friend,

Rory

_____________________________________________________________________________________________________________________________

 

Dear Rory,

It’s so hot here, like so, incredibly hot, that I think I might die. The only silver lining I can find is that at least it’s not as crowded as New York here. No sticky, sweaty train rides, no crowds of bumbling tourists taking up the whole sidewalk. There’s room to breathe. Is it like that in DC? You’re further south, so I’m assuming it’s hotter. Then again, you _are_ spending your time in all those nice, air-conditioned government buildings. My tax dollars at work, I suppose. Oh, geez, that sounded like Luke, didn’t it? I’m spending way too much time with him. He actually invited me to go fishing with him next weekend and (God help me) I said yes. Lorelai laughed herself silly when she heard about it. But I can tell it means a lot to Luke to do this kind of stuff with me. He thinks that if I turn out rotten, it’s his fault, even though he’s only had primary custody for just short of a year. I was pretty much fully formed when I got here.

I’m currently furiously working my way through my summer reading list, and when I say “my,” I mean Stars Hollow High School. In all the excitement of it being summer and all, it must have slipped my mind. I’m telling you this because I might have borrowed a few of your books to do said summer reading. I mean, come on, was I really gonna spend money on _The Great Gatsby_ and _Lord of the Flies_ (neither of which I’m too fond of)? Lorelai told me it was alright. Hell, she even told me where you keep the spare key. As if I’d need a key to get in. But at least all the red in my ledger is gone. Not so with everyone here, though.

I didn’t fight Dean, I swear. He came up to _me_. And we didn’t fight, per se. It was more of a spirited discussion. He said, and I quote, “I don’t know how you did it, but I guess you win, Jess.” There were some other choice phrases mixed in there, but that one was the gist of the whole conversation. Because I guess I did win, huh? It’s not often I get to say that, so I’ll say it again: I won. Gloating isn’t a good look on me, so I’ll leave it at that. Hey, at least he didn’t deck me.

You brought up Malibu Barbie and yes, while she does have her charms, she’s got nothing on some other girls I know.

 

-Jess

 

P.S. You asked me how I could be so sure of everything. I’m not sure of everything. I’m sure of you.

_____________________________________________________________________________________________________________________________

 

Dear Jess,

It’s hot here, too. It’s the humidity that really gets me, though. Like I’m swimming through the air. Like soup. It’s heavy and it makes me get into a really awful mood. Paris, too, and I know you’re wondering how she could get any worse, but she can. Trust me.  The amount of people (adults, even!) that she’s reduced to tears is reaching the triple digits.

But it doesn’t matter how hot it is here because I’m coming home soon! A week! Well, a week and a half. But it makes me feel better to say a week!  One week standing between me and Stars Hollow and Mom and you. Yes, you, Jess Mariano. God, it’s weird to think we’re friends. It’s weird to think that we’re maybe even more than friends. I’m guessing you want to jump immediately to the middle of things, but I like slow. I like having time to get used to things. But then I say all this and I’m thinking to myself, how could I need time to get used to Jess? The closest thing to a therapist I’ve ever had? That’s not all you are to me, but come on, I’m trying to keep things light. Whimsical, even, because I know that will drive you crazy.

I like you, Jess. A lot. And I think you’ve known that for a long time. Probably since we met. I don’t know how, but you did. It sort of scares me because you’re so guarded. The only time I’ve ever gotten you to say anything personal is through these letters and what if I can’t get you to open up in person? I don’t want it to be like me and Dean, except with the roles reversed. Dean was constantly mining me for information, like he thought he was going to be tested on all things Rory Gilmore. I kept a lot of things from him. I don’t want to play that part, the part of the person who is desperate to connect with someone who could care less. Which isn’t to say that I didn’t love Dean! I’m just….confused. I think I’ve said that a million times this summer. It’s the way things are changing. This is my last year at home, barring something terrible happening. I can’t imagine being away from my mom or Stars Hollow. It’s too weird to think about.

I’m glad you’re hanging out with Luke! His life seems so lonely sometimes. He needs a buddy. I know you’re making puking noises as you read this, but I don’t care. The more roots you put down, the less you’ll feel the need to run. You told me you were tired of running, didn’t you?

 

Your (something more than a) friend,

Rory

 

P.S. You better return my books in pristine condition, understand?

_________________________________________________________________________________________________________________________________

 

Dear Rory,

You like me. You _like_ me. _You_ like _me_. Sorry, I’m just in shock that I ever heard (read) those words from you. Took you long enough. I mean, my God, I spend a year pining after you and you act like we’re just two book-loving buddies. A dagger to my heart every time you smiled at me, Gilmore, a dagger to my heart. I pretty much stopped reading your letter after seeing those words, so forgive me if I neglect to mention any of the town’s latest tomfoolery.

Things are changing, you’re right about that. I can start vandalizing sidewalks again, give you a little something familiar to cling to when you get home. The townspeople still aren’t quite sure what to make of the new and improved Jess, but as long as they stop hassling Luke, I don’t care. Speaking of good behavior….I was promised a snowglobe. Are you gonna deliver on that?

A little less than a week. 5 days until you’re here, in the same place as me, and we can take things as slow as a Dean Martin torch song. Slower, even. We’ll do middle school dance rules: door at least 6 inches open and 3 feet on the floor at all times. Just come home before me and Lorelai go down there and drag you back ourselves.

 

Your (definitely more than a) friend,

Jess

 

P.S. I like you, too. Wasn’t sure if I ever actually said that to you, or if it was just implied. Well, I’m saying it now. I like you, Rory Gilmore. So, so much.

  



	4. September

Dear Jess,

I know I could have called or just tried to find you, but I’m so used to the letters, so I decided to scribble this on the back of a receipt I found in Mom’s car and leave it taped to the diner door. 

I’m home. Come find me as soon as you can. 

 

Your (impatient) friend,

Rory

___________________________________________________________________________________________________________________________________

 

Dear Rory,

Last night was great. Spectacular. Mind-blowing, even. I can’t believe you’re finally here and you’re finally kissing me. I mean, god, Gilmore, you practically made me disintegrate. How did Dean survive? How could he give you up? I’m just glad he did because now that I know what I’ve got, I’m not letting you go any time soon. 

Call me when you get this. I taped it to your window because I thought the chances of Lorelai finding it and reading it would be lower. 

 

-Jess

 

P.S. You know I’m kinda-sorta falling in love with you, right?

___________________________________________________________________________________________________________________________________

 

Dear Jess,

Yeah, I had an inkling that that was the case. That brooding rebel act you put on is shockingly transparent after a little making out. And I was worried I wouldn’t be able to get your guard down.

 

Your (girl)friend,

Rory

 

P.S. I’m kinda-sorta falling in love with you, too

  
  



End file.
